The Affairs

I’m a 35-year-old divorced man. I’ve been on plenty of dates since my marriage ended, but I invariably get asked this question on or before date #2: “Why did you get divorced?” This is where everything goes to shit. I’m honest: “We got divorced because I cheated on my wife. A lot.” This usually catches my date off guard because I’m “not the kind of guy I’d have thought could do that.” But I can hardly get past date #2 after this, because this information is “too much to handle.” Sometimes my dates will admit to having cheated too. Not even other cheaters are interested in seeing me again. I was a good husband and father for seven years. But after four sexless years of marriage, I strayed. Crying myself to sleep every night took its toll, and I self-medicated with casual sex with attractive women. Two years and 20 women later, I got caught. I don’t hide the facts; I own my mistakes. I’ve grown and learned from my mistakes. But it’s hard for most women to see past “cheater.” In my mind, anything less than complete honesty would validate the belief that I’m still a lying cheat. But complete honesty is kicking my ass and ruining potential relationships.

Forthright About Cheating, Then Silence

I’m going to give you the benefit of the doubt, FACTS, and assume that mistreatment, neglect, and stress didn’t extinguish your wife’s libido. (You weren’t shitty to your wife, right? You were helping with the kids, right?) I’m also going to assume that you made a good-faith effort to address the sexless state of your marriage before you began self-medicating with all those beautiful women. (You sought counseling and got medical checkups, right?) And I’m going to allow for the possibility that your wife may have married you under false pretenses, i.e., she wasn’t into sex or you or both, but she wanted marriage and kids and figured you would do. (I’m going to allow for that because that shit happens.)

These favorable assumptions—of the kind typically extended to persons seeking advice in a format like this—don’t exonerate you of all responsibility for cheating on your wife. But if they’re accurate, FACTS, they do put your cheating in a particular guilt-mitigating context.

And that’s what you need to do when you answer that question about why your marriage ended: Put your cheating in context. Most people intuitively understand that wedding vows aren’t sexual suicide pacts and are capable of feeling sympathy for those who find themselves in sexless marriages. But instead of emphasizing the context in which you cheated—the emotional dynamics of your marriage, those long sexless years—you’re emphasizing the breakdick pace at which you cheated and the quality of the pussy you landed.

“I cheated! A lot! With 20 beautiful women!” is one telling of the truth, FACTS, but it’s not the most flattering telling of the truth (for you) or the most comforting telling of the truth (for your date). Instead of saying, “I cheated with 20 women, all of them babes. I banged the living shit out of each and every one of them!” which makes you sound more boastful than remorseful, try saying something like this: “After four sexless years of marriage, I strayed. It was the wrong thing to do, but I was desperate. The cheating ended my marriage, which obviously needed to end, but it’s not something I ever want to do again.” Omit the detail about the number of women you cheated with while emphasizing your determination to avoid making the same mistake in your next committed relationship. Tell your date that you are looking for a strong sexual connection (and other things) with someone you can communicate with about sex (and other things). Because you’re not a cheater—not anymore.

I’m a 36-year-old heterosexual female who has been reading you for the better part of 20 years. That’s why when my formerly lovely husband descended into a hellish depression that turned our 10-year marriage into a loveless, sexless, miserable thing that I didn’t recognize, I knew what I had to do. I couldn’t get out for various financial, personal, and practical reasons, so I began an emotionally fulfilling, sanity-saving affair with a married man in the same situation. My emotional and sexual needs are getting met for the first time in years. The problem is that when we are together, my mind goes to how much I wish we could both chuck our marriages and be together all of the time, and I feel more miserable in my marriage because I can’t help comparing the two men in my life. Do you have any advice for keeping from mentally going to “happily ever after” when you are trying to stay balanced in marriage-saving-affair land?

Secret Affair Necessary Escape

An affair doesn’t come bundled with the same crap that a marriage does, SANE, so your time with Happy Affair Man isn’t burdened by mental and/or physical health crises, just as it’s not roughed up by ever-festering conflicts about money or chores or kids or all of the above. So let’s say you left Depressed Husband Man for Happy Affair Man, and he left his wife for you. How long would it be before you and Second Husband Man were facing down some similar crap or brand-new crap? Probably not long. You might be happier, but you won’t be happily-ever-after happier because no one ever is. The subject is moot, of course, if you’re not in a position to end your marriage and Happy Affair Man isn’t either.

I have been in a gay relationship for almost six years, and we are getting married in September. We are both predominantly tops, so we’ve been having threesomes for the majority of the time we’ve been together. About eight months ago, we had a threesome with someone who has since become a good friend. I have developed a strong bond with our third. My fiancé is not an overly affectionate person, and while I’ve had issues with that in the past and overlooked it, these past months have shown me how much I long for physical affection. My fiancé is threatened by the two of us showing affection. I reassure him as best I can, but nothing I say makes him feel less threatened by my wanting to have alone time with our third. I do not want to give up the bond I have with our third, and I have zero intention of leaving my fiancé. If we could help him get more comfortable, it could be a perfect situation for everyone, with all of our needs being met.

Sincerely Perplexed Lad In Triad

Seeing as your third sounds like a better match for you than your fiancé in several important ways—bottom to your top, more physically affectionate—I’m wondering why you wouldn’t want to dump the fiancé to run off with your third. Your fiancé is probably wondering the same thing. Unless your fiancé is willing to enter into a polyamorous triad, SPLIT, you’ll probably have to pick one or the other. And seeing as how you employ “we” in your last sentence—in reference to you and the third, not you and the fiancé—it sounds like you’ve already made your choice.

On the Lovecast, Dan chats with Seattle author Jason Schmidt about his memoir, A List of Things That Didn’t Kill Me.